ES2627738T3 - Un jarabe (met) acrílico líquido, su método de polimerización, uso y articulo moldeado obtenido del mismo - Google Patents

Un jarabe (met) acrílico líquido, su método de polimerización, uso y articulo moldeado obtenido del mismo Download PDF

Info

Publication number: ES2627738T3
Authority: ES; Spain
Prior art keywords: meth; acrylic; liquid; weight; mpa
Prior art date: 2013-04-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES14723364.7T

Other languages

English (en)

Spanish (es)

Inventor

Pierre Gerard

Daniel CALIN

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Arkema France SA

Original Assignee

Arkema France SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2013-04-25

Filing date

2014-04-25

Publication date

2017-07-31

2014-04-25 Application filed by Arkema France SA filed Critical Arkema France SA

2017-07-31 Application granted granted Critical

2017-07-31 Publication of ES2627738T3 publication Critical patent/ES2627738T3/es

Status Active legal-status Critical Current

2034-04-25 Anticipated expiration legal-status Critical

Links

NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 134
239000006188 syrup Substances 0.000 title claims abstract description 101
235000020357 syrup Nutrition 0.000 title claims abstract description 101
239000007788 liquid Substances 0.000 title claims abstract description 100
238000006116 polymerization reaction Methods 0.000 title claims abstract description 43
238000000034 method Methods 0.000 title claims description 37
239000000178 monomer Substances 0.000 claims abstract description 86
239000003999 initiator Substances 0.000 claims abstract description 45
-1 peroxy compound Chemical class 0.000 claims abstract description 40
229920000058 polyacrylate Polymers 0.000 claims abstract description 29
230000000977 initiatory effect Effects 0.000 claims abstract description 14
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 7
239000000758 substrate Substances 0.000 claims description 44
239000000835 fiber Substances 0.000 claims description 40
238000005470 impregnation Methods 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 27
238000004519 manufacturing process Methods 0.000 claims description 17
239000011347 resin Substances 0.000 claims description 14
229920005989 resin Polymers 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
238000002347 injection Methods 0.000 claims description 10
239000007924 injection Substances 0.000 claims description 10
150000003624 transition metals Chemical group 0.000 claims description 10
229910052723 transition metal Inorganic materials 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
239000010949 copper Substances 0.000 claims description 6
229910052802 copper Inorganic materials 0.000 claims description 6
238000001802 infusion Methods 0.000 claims description 5
238000000465 moulding Methods 0.000 claims description 5
230000000379 polymerizing effect Effects 0.000 claims description 5
229910052742 iron Inorganic materials 0.000 claims description 4
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 3
239000010941 cobalt Substances 0.000 claims description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
150000001451 organic peroxides Chemical class 0.000 claims description 3
239000012466 permeate Substances 0.000 claims description 3
238000010276 construction Methods 0.000 claims description 2
150000003623 transition metal compounds Chemical class 0.000 claims 1
150000004967 organic peroxy acids Chemical class 0.000 abstract description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 23
229920000642 polymer Polymers 0.000 description 14
229920001577 copolymer Polymers 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
239000004926 polymethyl methacrylate Substances 0.000 description 11
239000002131 composite material Substances 0.000 description 8
150000002978 peroxides Chemical class 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
239000002657 fibrous material Substances 0.000 description 6
238000001721 transfer moulding Methods 0.000 description 6
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical group CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 5
239000004342 Benzoyl peroxide Substances 0.000 description 5
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
235000019400 benzoyl peroxide Nutrition 0.000 description 5
239000007787 solid Substances 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
239000002557 mineral fiber Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
229920001169 thermoplastic Polymers 0.000 description 4
PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
239000004925 Acrylic resin Substances 0.000 description 3
229920000178 Acrylic resin Polymers 0.000 description 3
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
239000012190 activator Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
239000004744 fabric Substances 0.000 description 3
238000001746 injection moulding Methods 0.000 description 3
239000012263 liquid product Substances 0.000 description 3
239000002184 metal Substances 0.000 description 3
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000009736 wetting Methods 0.000 description 3
OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
229920000049 Carbon (fiber) Polymers 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
229920002522 Wood fibre Polymers 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
125000005250 alkyl acrylate group Chemical group 0.000 description 2
150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
239000004917 carbon fiber Substances 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000007547 defect Effects 0.000 description 2
239000003365 glass fiber Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
125000005395 methacrylic acid group Chemical class 0.000 description 2
239000004745 nonwoven fabric Substances 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
238000010133 reinforced reaction injection moulding Methods 0.000 description 2
230000002787 reinforcement Effects 0.000 description 2
238000001542 size-exclusion chromatography Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
239000002025 wood fiber Substances 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
UADCSAMCEHXQPQ-UHFFFAOYSA-N 2-tert-butylperoxycyclohexan-1-one Chemical compound CC(C)(C)OOC1CCCCC1=O UADCSAMCEHXQPQ-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
244000198134 Agave sisalana Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
240000000491 Corchorus aestuans Species 0.000 description 1
235000011777 Corchorus aestuans Nutrition 0.000 description 1
235000010862 Corchorus capsularis Nutrition 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
229920002430 Fibre-reinforced plastic Polymers 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
240000008790 Musa x paradisiaca Species 0.000 description 1
235000018290 Musa x paradisiaca Nutrition 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
DFPOZTRSOAQFIK-UHFFFAOYSA-N S,S-dimethyl-beta-propiothetin Chemical compound C[S+](C)CCC([O-])=O DFPOZTRSOAQFIK-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
SKYGTJFKXUWZMD-UHFFFAOYSA-N ac1l2n4h Chemical compound [Co].[Co] SKYGTJFKXUWZMD-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000000011 acetone peroxide Substances 0.000 description 1
235000019401 acetone peroxide Nutrition 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
235000005607 chanvre indien Nutrition 0.000 description 1
239000013626 chemical specie Substances 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
JAGNRFIVBRZDDN-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate;cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1.CC(=C)C(=O)OC1CCCCC1 JAGNRFIVBRZDDN-UHFFFAOYSA-N 0.000 description 1
229940124447 delivery agent Drugs 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
239000011487 hemp Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229940119545 isobornyl methacrylate Drugs 0.000 description 1
238000005304 joining Methods 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940100595 phenylacetaldehyde Drugs 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010107 reaction injection moulding Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004634 thermosetting polymer Substances 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
- B29C70/28—Shaping operations therefor
- B29C70/40—Shaping or impregnating by compression not applied
- B29C70/42—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Manufacturing & Machinery (AREA)
Reinforced Plastic Materials (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerisation Methods In General (AREA)

ES14723364.7T 2013-04-25 2014-04-25 Un jarabe (met) acrílico líquido, su método de polimerización, uso y articulo moldeado obtenido del mismo Active ES2627738T3 (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR1353796		2013-04-25
FR1353796A FR3005057B1 (fr)	2013-04-25	2013-04-25	Sirop liquide (meth)acrylique, son procede de polymerisation, son utilisation et objet moule obtenu a partir de celui-ci
PCT/EP2014/058500 WO2014174098A1 (en)	2013-04-25	2014-04-25	A liquid (meth) acrylic syrup its method of polymerization, use and molded article obtained thereof

Publications (1)

Publication Number	Publication Date
ES2627738T3 true ES2627738T3 (es)	2017-07-31

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ES14723364.7T Active ES2627738T3 (es)	2013-04-25	2014-04-25	Un jarabe (met) acrílico líquido, su método de polimerización, uso y articulo moldeado obtenido del mismo

Country Status (6)

Country	Link
US (1)	US10040889B2 (pl)
EP (1)	EP2989132B1 (pl)
ES (1)	ES2627738T3 (pl)
FR (1)	FR3005057B1 (pl)
PL (1)	PL2989132T3 (pl)
WO (1)	WO2014174098A1 (pl)

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FR3002941B1 (fr)	2013-03-08	2015-04-10	Arkema France	Sirop (meth)acrylique liquide d'impregnation d'un substrat fibreux, procede d'impregnation d'un substrat fibreux, materiau composite obtenu apres polymerisation dudit substrat pre-impregne
FR3016642B1 (fr) *	2014-01-22	2020-02-21	Arkema France	Procede d'impregnation pour un substrat fibreux, sirop monomere liquide pour le procede d'impregnation, sa methode de polymerisation et article structurel obtenu
FR3030547B1 (fr) *	2014-12-22	2018-08-17	Arkema France	Sirop (meth)acrylique liquide, procede d'impregnation d'un substrat fibreux par ledit sirop, et materiau composite obtenu apres polymerisation dudit sirop d'impregnation
FR3030546B1 (fr) *	2014-12-22	2018-04-06	Arkema France	Sirop (meth)acrylique liquide, procede d'impregnation d'un substrat fibreux par ledit sirop, et materiau composite obtenu apres polymerisation dudit sirop d'impregnation
FR3053350B1 (fr)	2016-06-29	2020-03-27	Arkema France	Composition liquide ou sirop comprenant un polymere a phases multiples et un polymere (meth)acrylique, sirop pour procede d'impregnation, procede d'impregnation pour un substrat fibreux, procede depolymerisation et article structure obtenu de celui-ci
FR3060577B1 (fr)	2016-12-21	2020-11-06	Arkema France	Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition
FR3064267B1 (fr) *	2017-03-27	2021-07-23	Arkema France	Compose reticulant, son procede de synthese, composition liquide comprenant ledit compose reticulant, son procede de polymerisation, et materiau obtenu apres polymerisation de ladite composition
FR3078537B1 (fr)	2018-03-05	2021-01-01	Arkema France	Composition de precurseur pour composites thermoplastiques acryliques et ses procedes de preparation et utilisation
FR3082845B1 (fr) *	2018-06-21	2021-01-15	Arkema France	Composition liquide comprenant trois initiateurs, son procede de polymerisation, son utilisation et materiau obtenu apres polymerisation de la composition
FR3083241B1 (fr) *	2018-06-28	2021-12-17	Arkema France	Composition (meth)acrylique, materiau composite obtenu a partir d'une telle composition, son procede de fabrication et ses utilisations
FR3087202B1 (fr)	2018-10-15	2021-11-26	Arkema France	Composition pour des compositions et composites polymeres (meth)acryliques, son procede de preparation et son utilisation
FR3105228B1 (fr) *	2019-12-18	2021-11-26	Arkema France	Composition comprenant un hemiperoxyacetal, son procédé de polymérisation, son utilisation et matériau de composition obtenu après polymérisation de la composition
WO2024099826A1 (en)	2022-11-07	2024-05-16	Covestro Deutschland Ag	Resin composition for preparing a thermoplastic polymer matrix
EP4406986A1 (en)	2023-01-24	2024-07-31	Covestro Deutschland AG	Resin composition for preparing a thermoplastic polymer matrix
FR3142762A1 (fr) *	2022-12-02	2024-06-07	Arkema France	Composition (meth)acrylique comprenant des matériaux recyclés, methode de production de ladite composition et ses utilisations

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FR3002940B1 (fr)	2013-03-08	2016-01-22	Arkema France	Sirop (meth)acrylique liquide d'impregnation d'un substrat fibreux et son procede de fabrication, procede d'impregnation d'un substrat fibreux, materiau composite obtenu apres polymerisation dudit substrat pre-impregne.
FR3002941B1 (fr)	2013-03-08	2015-04-10	Arkema France	Sirop (meth)acrylique liquide d'impregnation d'un substrat fibreux, procede d'impregnation d'un substrat fibreux, materiau composite obtenu apres polymerisation dudit substrat pre-impregne
FR3002942B1 (fr)	2013-03-11	2016-01-22	Arkema France	Sirop (meth)acrylique liquide d'impregnation d'un substrat fibreux, procede d'impregnation d'un substrat fibreux, materiau composite obtenu apres polymerisation dudit substrat pre-impregne.

2013
- 2013-04-25 FR FR1353796A patent/FR3005057B1/fr active Active
2014
- 2014-04-25 EP EP14723364.7A patent/EP2989132B1/en active Active
- 2014-04-25 ES ES14723364.7T patent/ES2627738T3/es active Active
- 2014-04-25 WO PCT/EP2014/058500 patent/WO2014174098A1/en not_active Ceased
- 2014-04-25 US US14/786,193 patent/US10040889B2/en active Active
- 2014-04-25 PL PL14723364T patent/PL2989132T3/pl unknown

Also Published As

Publication number	Publication date
US20160090434A1 (en)	2016-03-31
US10040889B2 (en)	2018-08-07
FR3005057A1 (fr)	2014-10-31
EP2989132B1 (en)	2017-03-08
FR3005057B1 (fr)	2015-05-15
EP2989132A1 (en)	2016-03-02
PL2989132T3 (pl)	2017-08-31
WO2014174098A1 (en)	2014-10-30

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ES2627738T3 (es)	2017-07-31	Un jarabe (met) acrílico líquido, su método de polimerización, uso y articulo moldeado obtenido del mismo
US10882966B2 (en)	2021-01-05	Liquid (meth)acrylic syrup for impregnating a fibrous substrate, method for impregnating a fibrous substrate, and composite material produced after polymerisation of said pre-impregnated substrate
CA2971550C (en)	2023-05-16	Liquid (meth)acrylic syrup, method for impregnating a fibrous substrate with said syrup, and composite material produced after polymerisation of said impregnation syrup
US10683405B2 (en)	2020-06-16	Liquid (meth)acrylic syrup for impregnating a fibrous substrate, method of impregnating a fibrous substrate, composite material obtained following polymerisation of the pre-impregnated substrate
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US11186723B2 (en)	2021-11-30	Liquid (meth)acrylic syrup, method for impregnating a fibrous substrate with said syrup, and composite material produced after polymerisation of said impregnation syrup
CN110088388B (zh)	2023-04-18	包含两种引发剂的液体组合物、其聚合方法、用途以及在组合物聚合后获得的材料或组合物
US11518866B2 (en)	2022-12-06	Peroxy ester cure of liquid prepolymer compositions
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CN110382570A (zh)	2019-10-25	用于本体单体聚合的空气空隙控制组合物
BR112021017851B1 (pt)	2025-12-23	Composição líquida lc1, processo para preparar a composição líquida lc1, uso da composição líquida lc1, processo para a fabricação de peças termoplásticas, processo para a fabricação de peças compósitas termoplásticas, material compósito polimérico e peça mecânica ou elemento estrutural
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